EP0020773B1 - Composition polymere sensible a la lumiere - Google Patents

Composition polymere sensible a la lumiere Download PDF

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Publication number
EP0020773B1
EP0020773B1 EP79901257A EP79901257A EP0020773B1 EP 0020773 B1 EP0020773 B1 EP 0020773B1 EP 79901257 A EP79901257 A EP 79901257A EP 79901257 A EP79901257 A EP 79901257A EP 0020773 B1 EP0020773 B1 EP 0020773B1
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EP
European Patent Office
Prior art keywords
group
formula
photosensitive
weight
polymer composition
Prior art date
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Expired
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EP79901257A
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German (de)
English (en)
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EP0020773A1 (fr
EP0020773A4 (fr
Inventor
Fusaji Shoji
Issei Takemoto
Hitoshi Yokono
Tokio Isogai
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Hitachi Ltd
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Hitachi Ltd
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Priority claimed from JP11921878A external-priority patent/JPS5545747A/ja
Priority claimed from JP11921978A external-priority patent/JPS5545748A/ja
Priority claimed from JP54043022A external-priority patent/JPS5839447B2/ja
Application filed by Hitachi Ltd filed Critical Hitachi Ltd
Publication of EP0020773A1 publication Critical patent/EP0020773A1/fr
Publication of EP0020773A4 publication Critical patent/EP0020773A4/fr
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Classifications

    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G73/00—Macromolecular compounds obtained by reactions forming a linkage containing nitrogen with or without oxygen or carbon in the main chain of the macromolecule, not provided for in groups C08G12/00 - C08G71/00
    • C08G73/06—Polycondensates having nitrogen-containing heterocyclic rings in the main chain of the macromolecule
    • C08G73/10—Polyimides; Polyester-imides; Polyamide-imides; Polyamide acids or similar polyimide precursors
    • C08G73/12—Unsaturated polyimide precursors
    • C08G73/121—Preparatory processes from unsaturated precursors and polyamines
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G73/00—Macromolecular compounds obtained by reactions forming a linkage containing nitrogen with or without oxygen or carbon in the main chain of the macromolecule, not provided for in groups C08G12/00 - C08G71/00
    • C08G73/06—Polycondensates having nitrogen-containing heterocyclic rings in the main chain of the macromolecule
    • C08G73/10—Polyimides; Polyester-imides; Polyamide-imides; Polyamide acids or similar polyimide precursors
    • C08G73/1003—Preparatory processes
    • C08G73/1007—Preparatory processes from tetracarboxylic acids or derivatives and diamines
    • C08G73/1025—Preparatory processes from tetracarboxylic acids or derivatives and diamines polymerised by radiations
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G73/00—Macromolecular compounds obtained by reactions forming a linkage containing nitrogen with or without oxygen or carbon in the main chain of the macromolecule, not provided for in groups C08G12/00 - C08G71/00
    • C08G73/06—Polycondensates having nitrogen-containing heterocyclic rings in the main chain of the macromolecule
    • C08G73/10—Polyimides; Polyester-imides; Polyamide-imides; Polyamide acids or similar polyimide precursors
    • C08G73/1042—Copolyimides derived from at least two different tetracarboxylic compounds or two different diamino compounds
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G73/00—Macromolecular compounds obtained by reactions forming a linkage containing nitrogen with or without oxygen or carbon in the main chain of the macromolecule, not provided for in groups C08G12/00 - C08G71/00
    • C08G73/06—Polycondensates having nitrogen-containing heterocyclic rings in the main chain of the macromolecule
    • C08G73/10—Polyimides; Polyester-imides; Polyamide-imides; Polyamide acids or similar polyimide precursors
    • C08G73/14—Polyamide-imides
    • G—PHYSICS
    • G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
    • G03F—PHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
    • G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
    • G03F7/004—Photosensitive materials
    • G03F7/038—Macromolecular compounds which are rendered insoluble or differentially wettable
    • G03F7/0387—Polyamides or polyimides

Definitions

  • the present invention relates to a new photosensitive polymer composition and to a support having thereon a cured film of this polymer composition.
  • photosensitive polyimide there have so far been known (a) the one prepared by coating a base plate with a mixture of 95-99 wt% of a polyamide acid type intermediate and 1-5 wt% of a dichromate, the coating being then irradiated with ultraviolet light, developed, if necessary, with hexamethylphosphoramide, and heated at 250°C (US-A-3623870), and (b) the other one prepared by coating a base plate with a polyamide acid intermediate having a photosensitive group in the molecule, the coating being then cured in the same way as in the case of (a) (DE-A-2308830).
  • composition (a) has difficulty of handling due to instability of said mixture and problem of insulating properties due to the remaining dichromate in the cured coating.
  • composition (b) it was necessary to use pure materials (1) and (2) below in case, for example, where said photosensitive polyamide acid intermediate is synthesized by addition polycondensation or by polycondensation of an isomeric mixture of dicarboxylic acid dichloride derivatives represented by the following formula (1) having photosensitive groups
  • the object of this invention is to provide an inexpensive composition of photosensitive polymer without any of such disadvantages of the prior arts and to provide cured film thereof formed on a supporting material.
  • the photosensitive polymer composition of the present invention is a blend of a photosensitive polyamide acid intermediate solution and a sensitizer therefor, the solution containing 0.1 to 40% by weight of the polyamide acid and 99.9 to 60% by weight of an organic solvent, and the polyamide acid and sensitizer being present in a ratio of 80 to 99.5% by weight of the polyamide acid to 20 to 0.5% by weight of the sensitizer, the polyamide acid having constituent units of the formula:
  • the photosensitive polymer composition may be processed by irradiation with ultraviolet light to bind the photosensitive polyamide acid intermediate molecules with one another into crosslinked molecules and further heating the resulting composition to about 200°C or more, preferably at 200-350°C (where heating between 200 and 350°C is carried out in an inert gas), to transform the composition into a polyimide through the intra-molecular dehydrating reaction.
  • the intrinsic viscosity of said polyamide acid intermediate used is at least 0.05, preferably 0.1-5.0 wherein the intrinsic viscosity is calculated according to the following equation through the determination of viscosities at 30°C of N,N-dimethylacetamide solution containing 0.5% of the photosensitive polyamide acid intermediate and of N,N-dimethylacetamide (solvent): (where C is the concentration of the photosensitive polyamide acid intermediate in gram/1 00 ml of the solution).
  • the melting point of the photosensitive polyamide acid intermediate having such a value of intrinsic viscosity does not indicate a fixed value.
  • the photosensitive polymer composition of this invention can be prepared in the following way: Either a mixture (the first compound) of 100-5 wt% of a diamine having a photosensitive group and 0-95 wt% of a diamine having no photosensitive group or at least one compound (the second compound) selected from the tetracarboxylic acid dianhydrides and the tricarboxylic anhydride monohalides is dissolved in an inert organic solvent sufficiently as completely as possible. While the temperature of the reaction system is kept below about 80°C, preferably at room temperature or less, another component is added thereto and the mixture is stirred.
  • reaction proceeds fast and the viscosity of the reaction mixture increased gradually with formation of a photosensitive polyamide acid intermediate, giving its solution in an inert organic solvent.
  • a sensitizer is added thereto (in a ratio of 80-99.5 wt% of the intermediate to 0.5-20 wt% of the sensitizer) to make up the photosensitive polymer composition.
  • a polyamide film-bearing material is prepared according to the invention by applying the photosensitive composition to a support, irradiating the resulting coating with ultraviolet light and heating to transform the irradiated coating into a polyimide film.
  • the photosensitive polymer composition applied to the support suitably is dried (preferably at a temperature below 100°C; any heating means can be applied) to vaporize the solvent, and thereafter irradiated with ultraviolet light and further heated at least at 200°C.
  • a suitable mask is placed on the coating and the system is irradiated with ultraviolet light, subsequently treated with a developer and a rinsing liquid, and further heated at least at 200°C.
  • Irradiation with ultraviolet light can be carried out, for example, by means of 1 kW high-voltage mercury lamp, but any other light source that generates actinic ray can be used.
  • the intensity of the incident light suitably is 3-50 mW/cm 2 and the time of exposure can be 30 sec to 10 min.
  • the reason for specifying the blending ratio of the diamine having a photosensitive group to the diamine having no photosensitive group as 100-5 wt% of the former to 9-95 wt% of the latter is due to the fact that, when the latter content exceeds 95 wt%, the photosensitive polymer composition is less sensitive to ultraviolet light and at the same time the resistance against a developer, of the portions exposed to ultraviolet irradiation is poorer.
  • the reason for specifying the preferred blending ratio of the diamine having a photosensitive group to the diamine having no photosensitive group as 100-60 wt% of the former to 0-40 wt% of the latter is due to the fact that this range gives best sensitivity and best resistance against a developer.
  • carboxylic acid dianhydride there are mentioned, for example, dianhydride of pyromellitic acid, 2,2-bis(3,4-dicarboxyphenyl) propane, bis(3,4-dicarboxyphenyi) ether, bis(3,4-dicarboxyphenyl) sulfone, 3,3',4,4'-benzophenone tetracarboxylic acid, 3,3',4,4'-biphenyltetracarboxylic acid, 2,2',3,3'-biphenyltetracarboxylic acid, 1,2,5,6-naphthalene tetracarboxylic acid, 2,3,6,7-naphthalene tetracarboxylic acid, 3,4,9,10-perytene tetracarboxylic acid, 2,2',6,6'-biphenyl tetracarboxylic acid and 1,3-bis(3,4-dicarboxyphenyl) hexafluoro
  • tricarboxylic acid anhydride monohalide there are mentioned, for example, monohalides of the following compounds such as trimellitic anhydride, 2,3,6-naphthalene tricarboxylic anhydride, 2,3,5-naphthalene tricarboxylic anhydride, 2,2',3-biphenyl tricarboxylic anhydride, 3,4,4'-biphenyl tricarboxylic anhydride, 2-(3,4-dicarboxyphenyl)-2-(3-carboxyphenyl) propane anhydride, 1,2,4-naphthalene tricarboxylic anhydride, 1,4,5-naphthalene tricarboxylic anhydride, 2-(2,3-dicarboxyphenyl)-2-(3-carboxyphenyl) propane anhydride, 1-(2,3-dicarboxyphenyl)-1-(3-carboxyphenyl) ethane anhydride, 1-(3,4-dicar
  • a first compound comprising a diamine having a photosensitive group and a diamine having no photosensitive group in a ratio of 100-5 wt% to 0-95 wt%, preferably 100-60 wt% of the former to 0 ⁇ 40 wt% of the latter is blended with an equivalent amount of a second compound consisting of at least one compound selected from tetracarboxylic dianhydrides and tricarboxylic anhydride monocarboxylic acid halides, the polymerization degree of the photosensitive polyamide acid intermediate is favorably larger, but it is unobjectionable to use either of the first and second compounds in somewhat excess amount.
  • the inert organic solvent used is required to be capable of dissolving all components of the first and second compounds mentioned above.
  • a particularly favorable one is a solvent capable of dissolving the resulting photosensitive polyamide acid intermediate, such as, for example, N-methyl-2-pyrrolidone, 1,3-dimethyl-2-imidazolidinone, N,N-dimethylacetamide, N-methylformamide, N,N-dimethylformamide, dimethyl sulfoxide, hexamethylphosphoramide, tetramethyjene sulfone, dimethyl sulfone, pyridine, tetramethylurea and N-acetyl-2-pyrrolidone.
  • solvents can be used each alone or in combination with one another or with a solvent such as benzene, toluene, nitrotoluene, chlorobenzene or cyclohexanone added.
  • a solvent such as benzene, toluene, nitrotoluene, chlorobenzene or cyclohexanone added.
  • the amount of the solvent used for the polymerization it should be such that the solute content in the resulting solution is in the range from 0.1 to 40 wt%. In this way a high molecular weight photosensitive polyamide acid intermediate can usually be obtained.
  • the photosensitive polymer composition of this invention contains a sensitizer.
  • a sensitizer though the stability of the composition depends on the kind of the photosensitive group, the composition is always stable under the light-shielded condition at room temperature. It is also possible to add a stabilizer such as, for example, hydroquinone or tert-butyl catechol, to increase the stability.
  • At least one of sensitizers such as the following examples may be used: anthraquinone, 2-methylanthraquinone, 2-ethylanthraquinone, benzoquinone, 1,2-naphthoquinone, 1,4-naphthoquinone, 1,2-benzoanthraquinone, acetophenone, benzophenone, p,p'-diaminobenzophenone, p,p'-dimethylamino benzophenone, p;p'-tetramethyldiaminobenzophenone (Michler's ketone), 2-nitrofluorene, 5-nitroace- naphthene, 4-nitro-l-naphthyiamine, N-acetyl-4-nitro-1-naphthylamine, p-nitroaniline, 2-chloro-4-nitroaniline, pycramide, 2-t-butylanthraquinone, 1,2-benz
  • the blending ratio of the sensitizer to the photosensitive polyamide acid intermediate is 0.5-20 wt% of the former to 80-99.5 wt% of the latter.
  • the sensitizer content is less than 0.5 wt%, the sensitizing effect does not appear, while, if the content exceeds 20 wt%, an adverse effect appears on the characteristics of the cured film.
  • the photosensitive polymer of this invention may be incorporated with a dyestuff, a pigment, or a colorant.
  • the supports usable in this invention are, for example, metals, glass, semiconductors (for example, silicon wafer and germanium wafer), ceramics, plastics, paper, conductive films (for example, In 2 O 3 ), metal oxide insulators (for example, TiO z' Ta 2 O 5 , silicon oxides), silicon nitride, and conductors.
  • the application of the photosensitive polymer composition on an above-said support is carried out by a usual means such as spinner coating, immersion, spraying, printing or the like.
  • Such application means are chosen according to the solid concentration and viscosity of the photosensitive polymer composition.
  • the cured film thickness can be controlled by application means, and the solid concentration and viscosity of the photosensitive polymer composition.
  • the development after irradiation with ultraviolet light, of the coating on the support is carried out by a polymerization solvent such as, for example, N-methyl-2-pyrrolidone, N,N-dimethylacetoamide or N,N-dimethylformamide.
  • a polymerization solvent such as, for example, N-methyl-2-pyrrolidone, N,N-dimethylacetoamide or N,N-dimethylformamide.
  • a solvent can optionally be used in incorporation with acetone or ethanol.
  • the rinsing liquid serves to wash away the developer solvent and it is preferable to use as the rinsing liquid a solvent such as toluene, acetone or ethanol, which is relatively well compatible with the developer solvent.
  • Example 1 does not illustrate the invention but is retained as a Reference Example for Example 2).
  • the intrinsic viscosity of the photosensitive polyamide acid intermediate thus obtained was 0.85 (0.5% N,N-dimethylacetamide solution at 30°C).
  • the viscosity of said photosensitive polymer composition was adjusted to 1000 m Pa.s (25°C), and the resulting composition was applied on a silicon wafer by means of a spinner.
  • the coated wafer was dried at 80°C for 40 minutes to volatilize the solvent away and to complete the coating.
  • This coating was covered with a mask having a desired pattern and irradiated with ultraviolet light at an incident beam intensity of 20 mW/cm 2 for 5 minutes by the use of a high-voltage mercury lamp to give a crosslinked polyamide acid coating.
  • the crosslinked coating was developed with a mixture of 3 volumes of N-methyl-2-pyrrolidone and 1 volume of ethanol and washed with a rinsing liquid (ethanol). Thereafter, the crosslinked coating was heated at 250°C for 60 minutes to give a polyimide coating pattern.
  • This coating was flat and uniform (good coating quality), and the precision of the pattern was also good.

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  • Chemical & Material Sciences (AREA)
  • Health & Medical Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Organic Chemistry (AREA)
  • Physics & Mathematics (AREA)
  • Spectroscopy & Molecular Physics (AREA)
  • General Physics & Mathematics (AREA)
  • Macromolecular Compounds Obtained By Forming Nitrogen-Containing Linkages In General (AREA)

Abstract

Composition polymere sensible a1a lumiere obtenue par l'addition d'un agent de sensibilisation a une solution dans un solvant organique inerte d'un intermediaire acide polyamide sensible a la lumiere obtenu par reaction d'un premier compose comprenant de 100 - 5% en poids d'une diamine presentant un groupe sensible a la lumiere et 0-95% en poids d'une diamine ne presentant pas de groupe sensible a la lumiere avec un second compose comprenant au moins un compose choisi parmi les dianhydrides d'acide tetracarboxylique et un monohalogenure d'anhydride d'acide tetracarboxylique dans un solvant organique inerte; et un support recouvert d'un film de polyamide forme par application de la composition a un support suivi par une irradiation avec des rayons UV et chauffage.

Claims (6)

1. Composition polymère photosensible, caractérisée en ce qu'il s'agit d'un mélange d'une solution d'un produit intermédiaire acide de polyamide photosensible et d'un agent sensibilisant pour cette solution, cette solution contenant 0,1 à 40% en poids de l'acide de polyamide et 99,9 à 60% en poids d'un solvant organique, l'acide polyamide et l'agent sensibilisant étant présents en un rapport de 80 à 99,5% en poids de l'acide de polyamide à 20 à 0,5% en poids de l'agent sensibilisant, l'acide comportant des unités constitutives ayant pour formule:
Figure imgb0087
et en option également des unités constitutives ayant pour formule:
Figure imgb0088
et étant obtenu par réaction, dans un solvant inerte, de 1 ) 100-5% en poids d'une diamine possédant un groupe photosensible de formule:
Figure imgb0089
et 0-95% en poids d'une diamine ne comportant aucun groupe photosensible, ayant pour formule:
Figure imgb0090
et 2) au moins un composé d'un dianhydride d'acide tétracarboxylique ayant pour formule:
Figure imgb0091
et d'un monohalogénure d'anhydride d'acide tricarboxylique ayant pour formule:
Figure imgb0092
formules dans lesquelles R1 est un groupe tétravalent comportant au moins 2 atomes de carbone, R2 est un groupe photosensible, R3 est un groupe bivalent possédant au moins 2 atomes de carbone, les deux groupes amino de la formule (II) étant liés à différents atomes de carbone dans R3,
R4 est un groupe tétravalent possédant au moins 4 atomes de carbone,
R5 est un groupe trivalent possédant au moins 2 atomes de carbone, X est de l'hydrogène ou un groupe ―Y―R2, Y est ―CONH―, ―CO―, ―O― ou ―CH2O― et Z est un atome d'un halogène.
2. Composition polymère photosensible selon la revendication 1, dans laquelle lorsque Y est -CONH-,
Figure imgb0093
ou
Figure imgb0094
Lorsque Y est -
Figure imgb0095
et lorsque Y est
Figure imgb0096
ou
Figure imgb0097
R6 étant un groupe alcoylidène ou un groupe hydroxyalcolidène, R7 est de l'hydrogène ou un groupe méthyle, R8 est de l'hydrogène ou un groupe cyano et R9 est de l'hydrogène, un atôme d'un halogène, un groupe alcoyle ou un groupe alcoxy.
3. Composition polymère photosensible selon la revendication 1, dans laquelle la diamine (I) a pour formule:
Figure imgb0098
Figure imgb0099
Figure imgb0100
Figure imgb0101
Figure imgb0102
Figure imgb0103
ou
Figure imgb0104
où Y et R2 sont tels que définis dans la revendication 1 ou 2, et, lorsque Y est -CONH- ou -CO-, R' est:
Figure imgb0105
et, lorsque Y est -0- ou -CH20-, R' est:
Figure imgb0106
ou a pour formule:
Figure imgb0107
Figure imgb0108
Figure imgb0109
Figure imgb0110
Figure imgb0111
Figure imgb0112
Figure imgb0113
Figure imgb0114
Figure imgb0115
Figure imgb0116
ou
Figure imgb0117
Où R' est
Figure imgb0118
et
Figure imgb0119
4. Composition polymère photosensible selon la revendication 1, 2 ou 3, dans laquelle la diamine de formule (I) et la diamine de formule (II) sont utilisées en une proportion de 100 à 60% en poids et 0 à 40% en poids respectivement.
5. Matériau de support de pellicule de polyamide, préparé par application d'une composition polymère photosensible revendiquée dans l'une quelconque des revendications précédentes, sur un support, irradiation du revêtement résultant à l'aide d'une lumière ultra-violette et chauffage en vue de transformer le revêtement irradié en une pellicule de polyimide.
6. Matériau de support de pellicule de polyamide selon la revendication 5, dans laquelle ledit support est un semiconducteur, un isolant formé d'un oxyde métallique, du verre, une céramique, un matériau conducteur ou un métal. _
EP79901257A 1978-09-29 1980-04-22 Composition polymere sensible a la lumiere Expired EP0020773B1 (fr)

Applications Claiming Priority (6)

Application Number Priority Date Filing Date Title
JP119218/78 1978-09-29
JP11921878A JPS5545747A (en) 1978-09-29 1978-09-29 Photosensitive polymer and its production
JP119219/78 1978-09-29
JP11921978A JPS5545748A (en) 1978-09-29 1978-09-29 Photosensitive polymer and its production
JP54043022A JPS5839447B2 (ja) 1979-04-11 1979-04-11 新規感光性重合体
JP43022/79 1979-04-11

Publications (3)

Publication Number Publication Date
EP0020773A1 EP0020773A1 (fr) 1981-01-07
EP0020773A4 EP0020773A4 (fr) 1981-02-20
EP0020773B1 true EP0020773B1 (fr) 1984-08-08

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EP (1) EP0020773B1 (fr)
DE (1) DE2967162D1 (fr)
WO (1) WO1980000706A1 (fr)

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WO1980000706A1 (fr) 1980-04-17
EP0020773A1 (fr) 1981-01-07
US4321319A (en) 1982-03-23
EP0020773A4 (fr) 1981-02-20
DE2967162D1 (en) 1984-09-13

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